EP0597672A2 - Composition d'encre noire d'un noir excellent - Google Patents

Composition d'encre noire d'un noir excellent Download PDF

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Publication number
EP0597672A2
EP0597672A2 EP93308939A EP93308939A EP0597672A2 EP 0597672 A2 EP0597672 A2 EP 0597672A2 EP 93308939 A EP93308939 A EP 93308939A EP 93308939 A EP93308939 A EP 93308939A EP 0597672 A2 EP0597672 A2 EP 0597672A2
Authority
EP
European Patent Office
Prior art keywords
group
ink composition
substituted
hydrogen atom
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP93308939A
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German (de)
English (en)
Other versions
EP0597672A3 (fr
EP0597672B1 (fr
Inventor
Miharu Yoshida
Hiroko Hayashi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Seiko Epson Corp
Original Assignee
Seiko Epson Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Seiko Epson Corp filed Critical Seiko Epson Corp
Publication of EP0597672A2 publication Critical patent/EP0597672A2/fr
Publication of EP0597672A3 publication Critical patent/EP0597672A3/fr
Application granted granted Critical
Publication of EP0597672B1 publication Critical patent/EP0597672B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes

Definitions

  • the present invention relates to an ink composition excellent in blackness and an inkjet recording method using the same.
  • a black ink is an important ink composition used as an inkjet recording ink composition for both monocolor and full color printings.
  • a general problem is to improve the water resistance of the print (for example, Japanese Patent Laid-Open Nos. 91577/1991, 226175/1992 and 233975/1992).
  • the ink composition described in these Japanese Patent Laid-Open No. 36279/1990 also leaves room for an improvement in the water resistance of the print.
  • ink compositions for an inkjet recording method Additional properties which are generally required of ink compositions for an inkjet recording method are that the ink does not clog jetting nozzles, printing can be quickly resumed even though clogging occurred, and ink properties remain unchanged during storage. Therefore, the ink compositions for ink jet recording should satisfy requirements of freedom from clogging of nozzles, quick resumption of printing after clogging of nozzles and excellent storage stability in addition to pure black color and water resistance.
  • an object of the present invention is to provide an ink composition excellent in blackness and storage stability and an inkjet recording method using the same.
  • Another object of the present invention is to provide an ink composition excellent in blackness even on plain paper and forming a sharp image and an inkjet recording method using the same.
  • Afurt her object of the present invention is to provide an inkcomposition capable of satisfying requirements of not only water resistance but also various properties required of ink compositions for inkjet recording, for example, no clogging of nozzles and excellent storage stability.
  • the present inventors have found that a combination of two dyes having a particular structure can provide an ink composition excellent in blackness, resumption of printing after clogging and storage stability.
  • the ink composition according to the present invention comprises a first dye represented by the general formula (I): wherein R 1 represents a phenyl or naphthyl group which may be substituted by a hydroxyl group, -NH 2 , -S0 3 M or-COOM wherein M represents a hydrogen atom or a cation species derived from an alkali metal, ammonia or an amine,
  • the first dye used in the ink composition according to the present invention is a compound represented by the general formula (I).
  • the compound represented by the general formula (I) is a dye that, as such, may be used as a dye for a black ink. In the present invention, it is added in combination with dyes, which will be described below, to provide an ink composition.
  • the phenyl group or naphthyl group as the R 1 may be unsubstituted or substituted.
  • the R 1 represents a substituted phenyl group, a monosubstituted (preferably 3- or4-substituted) phenyl group or a disubstituted (preferably 2,4-disubstituted or 3,5-disubstituted) phenyl group.
  • Preferred examples of the substituent include a hydroxyl group, -NH 2 , a sulfonic group and a carboxy group.
  • the sulfonic group and carboxy group may be in the form of a free acid or a salt.
  • Preferred examples of the salt include salts of sulfonic acid and carboxylic acid with an alkali metal, ammonia or amine (preferably tri(hydroxy C 1-6 alkyl)amine).
  • the naphthyl group as the R 1 may be 1- or 2-naphthyl and unsubstituted or substituted.
  • R 1 represents a substituted naphthyl
  • preferred examples of the substituent include those described above in connection with the phenyl group.
  • the carboxyalkyl group as the R 2 is preferably a carboxyC 1-6 alkyl group, still preferably a carboxy C 1-4 alkyl group.
  • the carboxy group preferably combines with an alkali metal or ammonia to form a salt.
  • the alkoxyalkyl group as the R 2 is preferably a C 1-6 alkoxyC 1-6 alkyl group, still preferably C1-4al- koxyC 1-4 alkyl group.
  • One or more hydrogen atoms present in the alkoxyalkyl group may be substituted, and preferred examples of the substituent include a hydroxyl group and -NH 2 .
  • the phenyl group as the R 2 may be substituted, and preferred examples of the substituent include a hydroxyl group and -NH 2 .
  • the alkanoyl group as the R 2 is preferably a C 1-6 alkanoyl group, still preferably C 1-4 alkanoyl group.
  • the R 3 , R 4 and R 5 may be the same or different and each independently represent a hydrogen atom or a sulfonic group.
  • the sulfonic group may be in the form of a free acid or a salt.
  • Preferred examples of the salt include salts of sulfonic acid with an alkali metal, ammonia or amine (preferably tri(hydroxy C 1 - 6 alkyl)amine).
  • the dyes represented by the general formula (I) can be produced by known methods and methods similar thereto.
  • the dyes represented by the general formula (I) can be produced by a method described in Japanese Patent Laid-Open No. 140270/1990 and Colour Index, Third Edition, the Society of Dyers and Colourists.
  • the second dye used in the ink composition of the present invention is a dye selected from the group consisting of C.I. Direct Yellow 86, 132 and 144 and compounds represented by the following general formulae (II) and (III).
  • C.I. Direct Yellow 86, 132 and 144 are described in, for example, Color Index, Third Edition.
  • the compounds represented by the general formula (II) are those that, as such, may be used as a dye.
  • the phenyl group or naphthyl group as the R 6 may be unsubstituted or substituted.
  • preferred examples of the substituent include a hydroxyl group, -NH 2 , a sulfonic group and a carboxy group.
  • the sulfonic group and carboxy group may be in the form of a free acid or a salt.
  • Preferred examples of the salt include salts of sulfonic acid and carboxylic acid with an alkali metal, ammonia or amine (preferably tri(hydroxy C 1-6 alkyl)amine).
  • the substituent is preferably located at the 3-or 4-posit ion.
  • the naphthyl group as the R 6 may be either 1-naphthyl or 2-naphthyl and unsubstituted or substituted.
  • R 1 represents a substituted naphthyl group
  • preferred examples of the substituent include those described above in connection with the phenyl group.
  • the dyes represented by the general formula (II) can be produced by known methods and methods similar thereto.
  • the dyes represented by the general formula (II) are described as an intermediate of black dyes in Japanese Patent Laid-Open No. 140270/1990 and can be produced according to a method described therein.
  • the compounds represented by the general formula (III) are those that, as such, may be used as a dye.
  • the alkyl group as the R 8 and R 9 is preferably a C 1-6 alkyl group, still preferably a C 1-4 alkyl group.
  • the hydroxyalkyl group as the R 8 and R 9 is preferably a hydroxy C 1-6 alkyl group, still preferably a hydroxy C 1-4 alkyl group.
  • Compounds represented by the general formula (III) wherein R 8 and R 9 simultaneously represent a hydrogen atom are excluded from the scope of the present invention.
  • the alkyl group as the R 10 and R 11 is preferably a C 1-6 alkyl group, still preferably a C 1-4 alkyl group.
  • the alkoxy group as the R 10 and R? 11 is preferably a C 1-6 alkoxy group, still preferably a C 1-4 alkoxy group.
  • the dyes represented by the general formula (III) can be produced by known methods and methods similar thereto.
  • the dyes represented by the general formula (III) can be produced by a method described in Japanese Patent Laid-Open No. 179100/1991 and Colour Index, Third Edition.
  • the content of the dye represented by the general formula (I) is preferably 0.1 to 10% by weight, still preferably 1 to 5% by weight.
  • the content of the dye represented by the general formula (I) is less than the above range, no satisfactory print density is often provided.
  • it exceeds the above range since the dissolution stability of the dye is deteriorated, clogging of nozzles often occurs.
  • the dyes represented by the general formula (I) may be added alone or in the form of a mixture of two or more of them.
  • an ink composition excellent in blackness can be provided by incorporating the first dye in combination with the second dye.
  • the content of C.I. Direct Yellow 86, 132 or 144 as the second dye is preferably in the range of from 0.001 to 0.5% by weight, still preferably in the range of from 0.005 to 0.4% by weight.
  • the content of the dye represented by the general formula (II) is preferably in the range of from 0.001 to 0.5% by weight, still preferably in the range of from 0.05 to 0.4% by weight.
  • the content of the dye represented by the general formula (III) in the ink composition according to the present invention is preferably in the range of from 0.005 to 0.5% by weight, still preferably in the range of from 0.01 to 0.04% by weight.
  • These second dyes may be added alone or in the form of a mixture of two or more of them.
  • the solvent for the ink composition of the present invention may be water or a mixed solvent comprising water and a water-soluble organic solvent, and the mixed solvent comprising water and a water-soluble organic solvent is preferred.
  • the water-soluble organic solvent used in the form of a mixture with water include lower alcohols, such as ethanol, 1-propanol and 2-propanol; polyhydric alcohols, such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol and glycerin; ethers of polyhydric alcohols, such as ethylene glycol monomethyl ether, diethylene glycol monobutyl ether and propylene glycol monoethyl ether; nitrogen-containing compounds, such as formamide, dimethylformamide, diethanolamine, triethanolamine, 1,3-dimethyl-2-imidazolidinone, 2-pyrrolidone and N-methyl-2-pyrrolidone; and sulfur-containing compounds, such as thiodiglycol and dimethylsulfoxide.
  • nitrogen-containing compounds such as 1,3-dimethyi-2-imidazoiidinone, 2-pyrrolidone and N-methyl-2-pyrrolidone
  • the amount of addition thereof is preferably in the range of from about 1 to 10% by weight.
  • triethanolamine is preferably in the range of from about 0.5 to 2% by weight from the viewpoint of color development of the dye and printing density.
  • dyes having a surface activity may be added to the ink composition of the present invention so far as the addition thereof is not detrimental to blackness of the ink and other effects.
  • the addition of dyes having a surface activity is advantageous.
  • the addition of such dyes having a surface activity can contribute to an improvement in the wettability of the recording head and ink path by the ink composition. As a result, bubbles, which have intruded into the recording head and ink path, can be easily discharged.
  • Specific examples of the dyes of this type include C.I. Direct Black 154 and 168.
  • various additives may be added to the ink composition of the present invention for the purpose of improving various properties of the ink composition.
  • resins, polymers, surfactants, pH adjustors, fungicides and ultraviolet absorbers may be added.
  • Ink compositions comprising components specified in the following Tables 1 to 5, that is, ink compositions of Examples A1 to A10, B1 to B10, C1 to C12, D1 to D10 and E1 to E11 and Comparative Examples A1 to A3, B1 to B3, C1 to C3, D1 to D3 and E1 to E3 were produced as follows. Specifically, individual components were mixed with each other, and the mixtures were filtered under pressure through a membrane filter having a pore diameter of 0.8 ⁇ m. Thereafter, the filtrates were deaerated with a vacuum pump to provide ink compositions.
  • the balance of the components consists of water.
  • recording paper (a) is an inkjet coat paper NM available from Mitsubishi Paper Mills, Ltd., recording paper (b) Cannon Dry available from Canon Sales Co., Inc., recording paper (c) Xerox 4024 available from Xerox Co., (d) Xerox P available from Fuji Xerox Co., Ltd. and recording paper (e) Recopy 6200 available from Ricoh Co., Ltd.
  • Tone of the 100% duty print samples on recording paper (a) to (e) was observed with the naked eye.
  • the criteria of the evaluation were as follows.
  • An inkjet printer HG-5130 was filled with the ink composition and allowed to stand at 40°C for one month without capping the recording head. Thereafter, the number of times of cleaning operation necessary for resuming normal printing was determined.
  • the criteria of the evaluation were as follows.
  • the ink composition was hermetically sealed in a glass vessel and allowed to stand at -30°C and 70°C for one month, and observation was effected on a change in the properties of the ink, a change in the tone and precipitation of insolubles after standing.
  • the results were evaluated as follows.
  • the print was observed with the naked eye to evaluate the sharpness of the image in terms of blurring and density according to the following criteria.
  • the 100% duty print samples were irradiated with light for 50 hr using a xenon fadeometer, and the change in the OD value between before irradiation and after irradiation was determined.
  • the results were evaluated as follows.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
EP93308939A 1992-11-09 1993-11-09 Composition d'encre noire d'un noir excellent Expired - Lifetime EP0597672B1 (fr)

Applications Claiming Priority (15)

Application Number Priority Date Filing Date Title
JP298856/92 1992-11-09
JP29885692 1992-11-09
JP29885692 1992-11-09
JP3572393 1993-02-24
JP3572493 1993-02-24
JP3572593 1993-02-24
JP3572493 1993-02-24
JP35723/93 1993-02-24
JP3572393 1993-02-24
JP3572593 1993-02-24
JP35724/93 1993-02-24
JP35725/93 1993-02-24
JP105579/93 1993-05-06
JP10557993 1993-05-06
JP10557993 1993-05-06

Publications (3)

Publication Number Publication Date
EP0597672A2 true EP0597672A2 (fr) 1994-05-18
EP0597672A3 EP0597672A3 (fr) 1994-10-26
EP0597672B1 EP0597672B1 (fr) 2001-06-13

Family

ID=27521724

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93308939A Expired - Lifetime EP0597672B1 (fr) 1992-11-09 1993-11-09 Composition d'encre noire d'un noir excellent

Country Status (3)

Country Link
US (1) US5439517A (fr)
EP (1) EP0597672B1 (fr)
DE (1) DE69330333T2 (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19541328A1 (de) * 1994-11-07 1996-05-09 Seiko Epson Corp Tintenzusammensetzung für die Tintenstrahl-Aufzeichnung
EP0859033A1 (fr) 1997-02-13 1998-08-19 Ilford Ag Colorants pour impression par jet d'encre
EP0919596A1 (fr) * 1997-12-01 1999-06-02 Bayer Aktiengesellschaft Colorants disazoiques
EP0924263A1 (fr) * 1997-10-03 1999-06-23 ILFORD Imaging Switzerland GmbH Colorants disazoiques, leur préparation et leur utilisation
US6068687A (en) * 1997-11-20 2000-05-30 Ilford Imaging Switzerland Gmbh Azo dyes and their preparation and use
WO2000046309A1 (fr) * 1999-02-05 2000-08-10 Ciba Specialty Chemicals Holding Inc. Encres pour coloration noire et utilisation
US6302949B1 (en) 1998-08-19 2001-10-16 Ilford Imaging Switzerland Gmbh Metallized bisazo dyes, their preparation and use
US6320031B1 (en) 1999-02-23 2001-11-20 Ilford Imaging Switzerland Gmbh Monoazo dyes and their preparation and use
US6562115B2 (en) 2000-05-30 2003-05-13 Ilford Imaging Switzerland Gmbh Azo dyes and their preparation and use
US6709502B2 (en) 2000-12-21 2004-03-23 Ilford Imaging Switzerland Gmbh Monoazo dyes and their preparation and use
WO2004029166A1 (fr) * 2002-09-25 2004-04-08 Fuji Photo Film Co., Ltd. Encre noire pour impression jet d'encre et procede d'impression jet d'encre
US6929688B2 (en) 2002-05-27 2005-08-16 Ilford Imaging Switzerland Gmbh Monoazo dyes and their preparation and use
US7060105B2 (en) 2002-09-26 2006-06-13 Ilford Imaging Switzerland Gmbh Copper complex monazo dyes and their preparation and use
EP1867685A1 (fr) 2006-06-13 2007-12-19 ILFORD Imaging Switzerland GmbH Colorants phthalocyanines, leur préparation et leur utilisation
EP1882723A1 (fr) 2006-07-27 2008-01-30 ILFORD Imaging Switzerland GmbH Colorants bisazoiques, leur préparation et leur utilisation
US7828886B2 (en) 2008-09-24 2010-11-09 Ilford Imaging Switzerland Gmbh Anthrapyridone dyes and their preparation and use
EP2468822A1 (fr) 2010-12-22 2012-06-27 ILFORD Imaging Switzerland GmbH Colorants noirs triazoïques, leur préparation et leur utilisation
WO2017092872A1 (fr) 2015-12-02 2017-06-08 Damien Moigno Colorants azoïques de type anthrapyridone, leur préparation et utilisation

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4434989A1 (de) * 1994-09-30 1996-04-04 Basf Ag Reaktive Azofarbstoffe mit einer Kupplungskomponente aus der Aminonaphthalinreihe
EP0757087B1 (fr) * 1995-07-14 1999-09-15 Mitsubishi Chemical Corporation Liquide d'enregistrement pour enregistrement par jet d'encre
US5728201A (en) * 1995-09-14 1998-03-17 Canon Kabushiki Kaisha Ink, and ink-jet recording method and instruments using the same
EP0771860B1 (fr) * 1995-11-02 2002-01-09 Seiko Epson Corporation Composition d'encre permettant une excellente réproduction du noir et procédé d'enregistrement par jet d'encre en faisant utilisation
GB9621224D0 (en) * 1996-10-11 1996-11-27 Zeneca Ltd Bisazo ink-jet dyes
GB9621225D0 (en) * 1996-10-11 1996-11-27 Zeneca Ltd Bisazo ink-jet dyes
JPH10279824A (ja) * 1997-03-31 1998-10-20 Nippon Kayaku Co Ltd 水溶性ジスアゾ化合物、水性インク組成物および着色体
DE69806585D1 (de) * 1997-04-01 2002-08-22 Avecia Ltd Tintenzusammensetzung enthaltend mindestens zwei azofarbstoffe
GB0005163D0 (en) * 2000-03-04 2000-04-26 Avecia Ltd Dye mixture
US6478862B1 (en) 2000-03-14 2002-11-12 Macdermid Acumen, Inc. Pigmented inks and a method of making pigmented inks
US6715868B2 (en) 2001-02-16 2004-04-06 Macdormid Colorspan, Inc. Direct dye inks and a method of making direct dye inks
JP4486810B2 (ja) * 2003-01-08 2010-06-23 富士フイルム株式会社 着色組成物及びインクジェット記録方法
US7056373B2 (en) * 2003-10-28 2006-06-06 Eastman Kodak Company Ink jet ink set
TW200718300A (en) * 2005-08-29 2007-05-01 Innovex Inc Polyester flex circuit constructions and fabrication methods for ink-resistant flex circuits used in ink jet printing
JP2008075028A (ja) * 2006-09-22 2008-04-03 Brother Ind Ltd インクジェット記録用インクセット
JP2008075029A (ja) * 2006-09-22 2008-04-03 Brother Ind Ltd インクジェット記録用インクセット
JP2008075031A (ja) * 2006-09-22 2008-04-03 Brother Ind Ltd インクジェット記録用インクセット
US7846245B2 (en) * 2006-11-02 2010-12-07 Hewlett-Packard Development Company, L.P. Ink-jet inks for neutral gray and black printing
US7887627B2 (en) * 2007-04-23 2011-02-15 Hewlett-Packard Development Company, L.P. Dye-based black ink formulations and ink-jet ink sets
JPWO2010146994A1 (ja) * 2009-06-17 2012-12-06 日本化薬株式会社 水溶性アゾ化合物又はその塩、インク組成物及び着色体
EP3015514B1 (fr) 2013-08-08 2017-02-01 Nippon Kayaku Kabushiki Kaisha Composition d'encre à base d'eau, procédé d'impression par jet d'encre et matériau coloré
WO2020137691A1 (fr) * 2018-12-27 2020-07-02 日本化薬株式会社 Composé azoïque ou son sel, et film et plaque de polarisation à base de colorant contenant chacun ce composé

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0168961A2 (fr) * 1984-06-14 1986-01-22 Taoka Chemical Co., Ltd Composition d'encre aqueuse
EP0359376A2 (fr) * 1988-07-26 1990-03-21 Canon Kabushiki Kaisha Liquide d'enregistrement et procédé d'enregistrement par jet d'encre faisant usage de ce liquide
EP0494523A1 (fr) * 1991-01-08 1992-07-15 Zeneca Limited Colorants disazoiques anioniques

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4626284A (en) * 1983-10-08 1986-12-02 Mitsubishi Chemical Industries Ltd. Recording liquid
US4725337A (en) * 1984-12-03 1988-02-16 Western Energy Company Method for drying low rank coals
US5203912A (en) * 1988-08-24 1993-04-20 Imperial Chemical Industries Plc Anionic dye
US4963189A (en) * 1989-08-24 1990-10-16 Hewlett-Packard Company Waterfast ink formulations with a novel series of anionic dyes containing two or more carboxyl groups
US5062893A (en) * 1990-06-22 1991-11-05 Hewlett-Packard Company Ink formulations by mixing anionic waterfast dyes containing two or more carboxyl groups
GB9016448D0 (en) * 1990-07-26 1990-09-12 Ici Plc Anionic compounds
GB9101544D0 (en) * 1991-01-24 1991-03-06 Ici Plc Compound

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0168961A2 (fr) * 1984-06-14 1986-01-22 Taoka Chemical Co., Ltd Composition d'encre aqueuse
EP0359376A2 (fr) * 1988-07-26 1990-03-21 Canon Kabushiki Kaisha Liquide d'enregistrement et procédé d'enregistrement par jet d'encre faisant usage de ce liquide
EP0494523A1 (fr) * 1991-01-08 1992-07-15 Zeneca Limited Colorants disazoiques anioniques

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19541328B4 (de) * 1994-11-07 2005-04-28 Seiko Epson Corp Tinten(Druckfarben)-Zusammensetzung
FR2726570A1 (fr) * 1994-11-07 1996-05-10 Seiko Epson Corp Composition d'encre pour enregistrement par jet d'encre
GB2294940A (en) * 1994-11-07 1996-05-15 Seiko Epson Corp Ink jet recording composition comprising glycerine, a pyrrolidone and a disazo dyestuff
US5647897A (en) * 1994-11-07 1997-07-15 Seiko Epson Corporation Ink composition for ink jet recording
GB2294940B (en) * 1994-11-07 1998-07-01 Seiko Epson Corp Ink jet ink comprising glycerine, a pyrollidone and a diazo dyestuff
DE19541328A1 (de) * 1994-11-07 1996-05-09 Seiko Epson Corp Tintenzusammensetzung für die Tintenstrahl-Aufzeichnung
EP0859033A1 (fr) 1997-02-13 1998-08-19 Ilford Ag Colorants pour impression par jet d'encre
US5989326A (en) * 1997-02-13 1999-11-23 Ilford Imaging Switzerland Gmbh Dyes for ink jet printing
US5969115A (en) * 1997-10-03 1999-10-19 Ilford Imaging Switzerland Gmbh Bisazo dyes and their preparation and use
EP0924263A1 (fr) * 1997-10-03 1999-06-23 ILFORD Imaging Switzerland GmbH Colorants disazoiques, leur préparation et leur utilisation
US6068687A (en) * 1997-11-20 2000-05-30 Ilford Imaging Switzerland Gmbh Azo dyes and their preparation and use
US6194554B1 (en) 1997-12-01 2001-02-27 Bayer Aktiengesellschaft Disazo dyes
EP0919596A1 (fr) * 1997-12-01 1999-06-02 Bayer Aktiengesellschaft Colorants disazoiques
US6302949B1 (en) 1998-08-19 2001-10-16 Ilford Imaging Switzerland Gmbh Metallized bisazo dyes, their preparation and use
WO2000046309A1 (fr) * 1999-02-05 2000-08-10 Ciba Specialty Chemicals Holding Inc. Encres pour coloration noire et utilisation
US6500247B1 (en) 1999-02-05 2002-12-31 Ciba Specialty Chemicals Corporation Black-dyeing inks and their use
US7057024B2 (en) 1999-02-05 2006-06-06 Ciba Specialty Chemicals Corporation Black-dyeing inks and their use
US6320031B1 (en) 1999-02-23 2001-11-20 Ilford Imaging Switzerland Gmbh Monoazo dyes and their preparation and use
US6562115B2 (en) 2000-05-30 2003-05-13 Ilford Imaging Switzerland Gmbh Azo dyes and their preparation and use
US6709502B2 (en) 2000-12-21 2004-03-23 Ilford Imaging Switzerland Gmbh Monoazo dyes and their preparation and use
US6929688B2 (en) 2002-05-27 2005-08-16 Ilford Imaging Switzerland Gmbh Monoazo dyes and their preparation and use
US7303272B2 (en) 2002-09-25 2007-12-04 Fujifilm Corporation Black ink for inkjet recording and inkjet recording method
EP1544260A4 (fr) * 2002-09-25 2006-02-08 Fuji Photo Film Co Ltd Encre noire pour impression jet d'encre et procede d'impression jet d'encre
EP1544260A1 (fr) * 2002-09-25 2005-06-22 Fuji Photo Film Co., Ltd. Encre noire pour impression jet d'encre et procede d'impression jet d'encre
WO2004029166A1 (fr) * 2002-09-25 2004-04-08 Fuji Photo Film Co., Ltd. Encre noire pour impression jet d'encre et procede d'impression jet d'encre
KR100825368B1 (ko) * 2002-09-25 2008-04-28 후지필름 가부시키가이샤 잉크젯 기록용 블랙 잉크 및 잉크젯 기록 방법
US7060105B2 (en) 2002-09-26 2006-06-13 Ilford Imaging Switzerland Gmbh Copper complex monazo dyes and their preparation and use
EP1867685A1 (fr) 2006-06-13 2007-12-19 ILFORD Imaging Switzerland GmbH Colorants phthalocyanines, leur préparation et leur utilisation
US7632345B2 (en) 2006-06-13 2009-12-15 Ilford Imaging Switzerland Gmbh Phthalocyanine dyes and their preparation and use
EP1882723A1 (fr) 2006-07-27 2008-01-30 ILFORD Imaging Switzerland GmbH Colorants bisazoiques, leur préparation et leur utilisation
US7828886B2 (en) 2008-09-24 2010-11-09 Ilford Imaging Switzerland Gmbh Anthrapyridone dyes and their preparation and use
EP2468822A1 (fr) 2010-12-22 2012-06-27 ILFORD Imaging Switzerland GmbH Colorants noirs triazoïques, leur préparation et leur utilisation
US8361168B2 (en) 2010-12-22 2013-01-29 Ilford Imaging Switzerland Gmbh Black trisazo dyes, their preparation and their use
WO2017092872A1 (fr) 2015-12-02 2017-06-08 Damien Moigno Colorants azoïques de type anthrapyridone, leur préparation et utilisation

Also Published As

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EP0597672A3 (fr) 1994-10-26
DE69330333T2 (de) 2001-10-11
EP0597672B1 (fr) 2001-06-13
US5439517A (en) 1995-08-08
DE69330333D1 (de) 2001-07-19

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